Awkward Moment Entusiast Pillows

Bring comfort and humor to their space with pillows featuring quirky designs and clever messages about life's awkward encounters. A cozy way to embrace every stumble with a smile.

All Products Prints T-Shirts Mugs Pillows

"Oh, ah, sorry!"

from $19.00

Showbiz Awards

from $19.00

'When you asked me over for a home-cooked meal, I assumed you'd be making it.'

'When you asked me over for a home-cooked meal, I assumed you'd be making it.' mockup

'When you asked me over for a home-cooked meal, I assumed you'd be making it.'

from $19.00

"I was a lot happier with the elephant in the room."

"I was a lot happier with the elephant in the room." mockup

"I was a lot happier with the elephant in the room."

from $19.00

Always an awkward moment when you meet a Dung Beetle...

Always an awkward moment when you meet a Dung Beetle... mockup

Always an awkward moment when you meet a Dung Beetle...

from $19.00

"Do you have a boyfriend?"

from $19.00

"If you think the first half of this psychological test is intrusive, wait until you're grilled by me mother."

"If you think the first half of this psychological test is intrusive, wait until you're grilled by me mother." mockup

"If you think the first half of this psychological test is intrusive, wait until you're grilled by me mother."

from $19.00

"A 'pregnant pause' is effective only if you've already said something."

"A 'pregnant pause' is effective only if you've already said something." mockup

"A 'pregnant pause' is effective only if you've already said something."

from $19.00

'Eh...our costume party was last Saturday!'

'Eh...our costume party was last Saturday!' mockup

'Eh...our costume party was last Saturday!'

from $19.00

"You and your daft inventions."

from $19.00

"I suppose I should have let a few minutes elapse between declaring my love for you and announcing that I also loved lobster."

"I suppose I should have let a few minutes elapse between declaring my love for you and announcing that I also loved lobster." mockup

"I suppose I should have let a few minutes elapse between declaring my love for you and announcing that I also loved lobster."

from $19.00

"Humiliation is a very important part of the the process, Mr. Keifer."

"Humiliation is a very important part of the the process, Mr. Keifer." mockup

"Humiliation is a very important part of the the process, Mr. Keifer."

from $19.00

"Let's start with a couple of glasses of water and if that goes well I'll order two coffees."

"Let's start with a couple of glasses of water and if that goes well I'll order two coffees." mockup

"Let's start with a couple of glasses of water and if that goes well I'll order two coffees."

from $19.00

"OK, I know that this is borderline inappropriate, but just hear me out ..."

"OK, I know that this is borderline inappropriate, but just hear me out ..." mockup

"OK, I know that this is borderline inappropriate, but just hear me out ..."

from $19.00

"Such a cute doggie! And I'll bet you make the cutest poopies too, don't you?"

"Such a cute doggie! And I'll bet you make the cutest poopies too, don't you?" mockup

"Such a cute doggie! And I'll bet you make the cutest poopies too, don't you?"

from $19.00

"Don't panic, she'll be back. We lock the washroom windows from the outside."

"Don't panic, she'll be back. We lock the washroom windows from the outside." mockup

"Don't panic, she'll be back. We lock the washroom windows from the outside."

from $19.00

"Ignore the screams, sir. I'll get a new fork."

"Ignore the screams, sir. I'll get a new fork." mockup

"Ignore the screams, sir. I'll get a new fork."

from $19.00

"Are you blushing?!"

from $19.00

"Good evening, I'm your date. Let me begin by saying I'm sorry I'm late, I'm sorry I'm bald and I'm sorry I'm short."

"Good evening, I'm your date. Let me begin by saying I'm sorry I'm late, I'm sorry I'm bald and I'm sorry I'm short." mockup

"Good evening, I'm your date. Let me begin by saying I'm sorry I'm late, I'm sorry I'm bald and I'm sorry I'm short."

from $19.00

Baldo's How to Be Uncool: No. 5. Forget how hot the coffee is while you're thinking how cool you look sitting in a coffee shop.

Baldo's How to Be Uncool: No. 5. Forget how hot the coffee is while you're thinking how cool you look sitting in a coffee shop. mockup

Baldo's How to Be Uncool: No. 5. Forget how hot the coffee is while you're thinking how cool you look sitting in a coffee shop.

from $19.00

"I'm sensing an awkward presence." mockup

"I'm sensing an awkward presence."

from $19.00

Speed Dating Disasters

from $19.00

"If that girl sent over a double cappuccino, maybe you should go talk to her!"

"If that girl sent over a double cappuccino, maybe you should go talk to her!" mockup

"If that girl sent over a double cappuccino, maybe you should go talk to her!"

from $19.00

"On a scale of 1-10, how painfully awkward is this?"

"On a scale of 1-10, how painfully awkward is this?" mockup

"On a scale of 1-10, how painfully awkward is this?"

from $19.00

As years of unspoken tension surfaced, Trunky refused to raise his hand like a coward.

As years of unspoken tension surfaced, Trunky refused to raise his hand like a coward. mockup

As years of unspoken tension surfaced, Trunky refused to raise his hand like a coward.

from $19.00

'Look. . . for the last time, I'm not playin' 'footsie' with you!'

'Look. . . for the last time, I'm not playin' 'footsie' with you!' mockup

'Look. . . for the last time, I'm not playin' 'footsie' with you!'

from $19.00

"You have to get up early tomorrow, too? We have so much in common!"

"You have to get up early tomorrow, too? We have so much in common!" mockup

"You have to get up early tomorrow, too? We have so much in common!"

from $19.00

"I think that one is a little too honest."

"I think that one is a little too honest." mockup

"I think that one is a little too honest."

from $19.00

"Of course mating is natural. It's just not the kind of thing you want to see your parents doing."

"Of course mating is natural. It's just not the kind of thing you want to see your parents doing." mockup

"Of course mating is natural. It's just not the kind of thing you want to see your parents doing."

from $19.00

"Let’s try another one. Jerry blinked, Kate’s giving Jon the finger, and Jess is choking."

"Let’s try another one. Jerry blinked, Kate’s giving Jon the finger, and Jess is choking." mockup

"Let’s try another one. Jerry blinked, Kate’s giving Jon the finger, and Jess is choking."

from $19.00

'It's our first date. You don't know me well enough to ask if I'm getting enough fiber.'

'It's our first date. You don't know me well enough to ask if I'm getting enough fiber.' mockup

'It's our first date. You don't know me well enough to ask if I'm getting enough fiber.'

from $19.00

Awkward Moment Entusiast Pillows Collection

Awkward Moment Entusiast Mugs

Explore our collection of mugs designed for awkward moment enthusiasts—full of witty quotes and funny cartoons perfect for starting the day with a smile.

Awkward Moment Entusiast Prints

Browse quirky prints that capture the humor of awkward moments—great for decorating a space that’s full of personality and fun.

Awkward Moment Entusiast T-Shirts

Discover t-shirts that celebrate the humor in life's awkward moments—ideal for a casual, fun-loving wardrobe update.